Substituted 2-phenylpyridine as herbicide

ABSTRACT

Substituted 2-phenylpyridines of formula I                    
     where R 1  to R 5  are described herein, 
     their use as herbicides and for the desiccation and/or defoliation of plants.

The present invention relates to novel substituted 2-phenyl-pyridines ofthe formula I

in which the variables have the following meanings:

n is zero or 1;

R¹ is mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylaminosulfonyl or di(C₁-C₆-alkyl)aminosulfonyl;

R²,R³ independently of one another are hydrogen or halogen;

R⁴ is cyano, hydroxyl, halogen, C₁-C₆-alkoxy or phenylmethoxy, it beingpossible for the phenyl ring to be unsubstituted or to have attached toit one to three substituents, in each case selected from the groupconsisting of hydroxyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, hydroxycarbonyl, (C₁-C₆-alkoxy)carbonyland (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy;

R⁵ is hydrogen, nitro, cyano, hydroxylamino, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, —COCl, —CO—OR⁶, —CO—N(R⁷)R⁸,—CO—O—(C₁-C₄-alkylene)—CO—R⁶—, —CO—O—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸,—X¹—(C₁-C₄-alkylene)—CO—R⁶, —X¹—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸, —X¹—R⁹, —CH═C(R¹⁰)—CO—OR⁶,—CH═C(R¹⁰)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CH═C(R¹⁰)—CO—N(R⁷)R⁸, formyl,—CO—R⁶,

 —C(R⁸)═N—OR¹⁵, —X¹—(C₁-C₄-alkylene)—C(R⁸)═N—OR¹⁵,—CH═C(R¹⁰)—C(R⁸)═N—OR¹⁵, —CH(C₁-C₆-alkoxy)₂, —N(R¹⁶)R¹⁷,—N(R¹⁶)—SO₂—(C₁-C₆-alkyl), —N(R¹⁶)—CO—(C₁-C₆-alkyl), chlorosulfonyl,hydroxysulfonyl or —SO₂—N(R¹⁸)R¹⁹;

R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or 3-oxetanyl;

R⁷ is hydrogen or C₁-C₆-alkyl;

R⁸ is hydrogen, hydroxyl, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,phenyl-C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or C₃-C₆-alkynyloxy or

R⁷ and R⁸ together are a tetra- or pentamethylene chain which can haveattached to it a (C₁-C₆-alkoxy)carbonyl radical;

R⁹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₃-C₆-cycloalkyl or C₁-C₆-alkoxy-C₁-C₆-alkyl;

R¹⁰ is hydrogen, halogen or C₁-C₆-alkyl;

R¹¹-R¹⁴ independently of one another are hydrogen, C₁-C₆-alkyl or(C₁-C₆-alkoxy)carbonyl;

R¹⁵ is hydrogen, C₁-C₆-alkyl, phenyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹⁶ is hydrogen or C₁-C₆-alkyl;

R¹⁷ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy;

R¹⁸ is hydrogen or C₁-C₆-alkyl;

R¹⁹ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy or

R¹⁸ and R¹⁹ together are a tetra- or pentamethylene chain which can haveattached to it a (C₁-C₆-alkoxy)carbonyl radical;

X¹-X³ independently of one another are oxygen or sulfur, and to theagriculturally useful salts of the compounds I where R⁶ =hydrogen.

Moreover, the invention relates to

the use of the compounds I as herbicides or for thedesiccation/defoliation of plants,

herbicidal compositions and compositions for the desiccation and/ordefoliation of plants which comprise the compounds I as activesubstances,

methods of controlling undesirable vegetation and for the desiccationand/or defoliation of plants using the compounds I,

processes for the preparation of the compounds I and of herbicidalcompositions and compositions for the desiccation and/or defoliation ofplants which make use of the compounds I, and to

intermediates of the formulae IIa, V and VI.

WO 95/02580 describes a large number of herbicidally active2-phenylpyridines. The general formula in this publication also embracessome of the present compounds I where R¹=C₁-C₄-alkylthio.

WO 94/05153 relates to herbicidally active benzene compounds which canalso have attached to them, inter alia, a pyridine ring which issubstituted by halogen and methylthio. However, the specificsubstitution pattern of the present 2-phenylpyridines cannot be found inthis publication.

DE-A 19 500 760, DE-A 19 500 758 and DE-A 19 500 911 already describecertain substituted 2-phenylpyridines of the type of the compounds Iwhere mercapto, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl orC₁-C₄-alkylsulfonyl occupy the 5-position of the pyridine ring asherbicidal and desiccant/defoliant active ingredients.

However, the herbicidal activity of the known compounds is not alwaysentirely satisfactory with regard to the harmful plants.

It is an object of the present invention to provide novel herbicidallyactive compounds with which undesirable plants can be controlled better,in a targeted fashion, than was possible to date. It was also an objectto provide novel compounds which have a desiccant/defoliant action.

We have found that this object is achieved by the substituted2-phenylpyridines of the formula I defined at the outset which have aherbicidal action, and by novel intermediates V and VI for theirpreparation.

We have furthermore found herbicidal compositions which comprise thecompounds I and which have a very good herbicidal activity. Moreover, wehave found processes for the preparation of these compositions andmethods for controlling undesirable vegetation using the compounds I.

Moreover, we have found that the compounds I are also suitable for thedefoliation/desiccation of parts of plants, suitable plants being cropplants such as cotton, potatoes, oilseed rape, sunflowers, soya beans orfield beans, in particular cotton and potatoes. Accordingly, we havefound compositions for the desiccation and/or defoliation of plants,processes for the preparation of these compositions, and methods for thedesiccation and/or defoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican have one or more chiral centers, in which case they are present asenantiomer or diastereomer mixtures. The invention relates not only tothe pure enantiomers or diastereomers, but also to mixtures of these.

The substituted 2-phenylpyridines I where R⁶=hydrogen can exist in theform of their agriculturally useful salts, the nature of the saltgenerally being of no importance. In general, suitable salts are saltsof those bases where the herbicidal activity is not adversely affectedin comparison with the free compound I.

Especially suitable salts are those of the alkali metals, preferablysodium and potassium salts, the alkaline earth metals, preferablycalcium and magnesium salts, those of the transition metals, preferablyzinc and iron salts, and also ammonium salts where the ammonium ion can,if desired, have attached to it one to four C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl substituents and/or a phenyl or benzyl substituent,preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium and trimethyl-(2-hydroxyethyl)ammonium salts,furthermore phosphonium salts, sulfonium salts such as, preferably,tri(C₁-C₄-alkyl)sulfonium salts, and sulfoxonium salts such as,preferably, tri(C₁-C₄-alkyl)sulfoxonium salts.

The organic moieties mentioned for the substituents R¹ and R⁴ to R¹⁹ oras radicals on a phenyl ring or on tetra- or pentamethylene arecollective terms for individual enumerations of the individual groupmembers. All carbon chains, ie. all alkyl, haloalkyl, phenylalkyl,alkylene, alkoxy, haloalkoxy, phenylalkoxy, alkylthio, alkylsulfinyl,alkylsulfonyl, hydroxycarbonylalkyl, alkoxycarbonyl, alkylamino,alkenyl, alkynyl, alkenyloxy and alkynyloxy moieties can bestraight-chain or branched. Halogenated substituents preferably haveattached to them one to five identical or different halogen atoms.

The meaning halogen is in each case fluorine, chlorine, bromine oriodine, in particular fluorine or chlorine.

Other examples of meanings are:

C₁-C₆-alkyl: C₁-C₄-alkyl such as CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl,CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ and C(CH₃)₃, or e.g. n-pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or1-ethyl-2-methylpropyl, in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂,n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₆-haloalkyl: a C₁-C₆-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. CH₂F, CHF₂, CF₃, CH₂Cl, CH(Cl)₂, C(Cl)₃, CHFCl, CF(Cl)₂,CF₂Cl, CF₂Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl,C₂—F₅, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl,2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, CF₂—C₂F₅,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl,4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl,5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undecafluoropentyl,6-fluorohexyl, 6-chlprohexyl, 6-bromohexyl, 6-iodohexyl,6,6,6-trichlorohexyl or dodecafluorohexyl, in particular CH₂F, CHF₂,CF₃, CH₂Cl, 2-fluoroethyl, 2-chloroethyl, 1,2-dichloroethyl,2,2,2-trifluoroethyl or C₂F₅;

phenyl-C₁-C₆-alkyl: eg. benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl,1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl,1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,1-benzyleth-1-yl, 1-benzyl-1-methyleth-1-yl, 1-benzylprop-1-yl or2-phenylhex-6-yl, in particular benzyl or 2-phenylethyl;

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, inparticular cyclopentyl or cyclohexyl;

C₁-C₄-alkylene: —CH₂—, —CH(CH₃)—, 1,2-ethylene, 1,1-propylene,1,2-propylene, 1,3-propylene, —C(CH₃)₂—, 1,1-butylene, 1,2-butylene,1,3-butylene, 1,4-butylene, 2,2-butylene, 2,3-butylene,2-methyl-1,1-propylene, 2-methyl-1,2-propylene or2-methyl-1,3-propylene, preferably methylene, 1,1-ethylene,1,2-ethylene, 1,1-propylene or 2,2-propylene;

C₁-C₆-alkoxy: eg. OCH₃, OC₂H₅, n-propoxy, OCH(CH₃)₂, n-butoxy,OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂, OC(CH₃)₃, n-pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy, in particular OCH₃, OC₂H₅, OCH(CH₃)₂ orOC(CH₃)₃;

C₁-C₆-haloalkoxy: C₁-C₆-alkoxy as mentioned above which is partially orfully substituted by fluorine, chlorine, bromine and/or iodine, eg.OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, OCHFCl, OCF(Cl)₂, OCF₂Cl,OCF₂Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, OC₂F₅, 2-fluoropropoxy, 3-fluoropropoxy,2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy,2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, OCF₂-C₂F₅, 1-(CH₂F)-2-fluoroethoxy,1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy,4-chlorobutoxy, 4-bromobutoxy, 5nonafluorobutoxy, 5-fluoropentoxy,5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy,6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy ordodecafluorohexyloxy;

phenyl-C₁-C₆-alkoxy: e.g. benzyloxy, 1-phenylethoxy, 2-phenylethoxy,1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy,1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy, 3-phenylbut-1-yloxy,4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy,3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy, 1-benzyleth-1-yloxy,1-benzyl-1-methyl-eth-1-yloxy, 1-benzylprop-1-yloxy or2-phenylhex-6-yloxy, in particular benzyloxy or 2-phenylethoxy;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted byC₁-C₆-alkoxy as mentioned above, eg. CH₂OCH₃, CH₂OC₂H₅, CH₂OCH₂—C₂H₅,CH₂OCH(CH₃)₂, CH₂OCH₂CH₂—C₂H₅, (1-propoxy)methyl,(2-methyl-propoxy)methyl, CH₂OC(CH₃)₃, CH₂O(CH₂)₃—C₂H₅, CH₂O(CH₂)₄—C₂H₅,CH(CH₃)OCH₃, CH(CH₃)OC₂H₅, CH₂CH₂OCH₃, CH₂CH₂OC₂H₅, CH₂CH₂OCH₂—C₂H₅,CH₂CH₂OCH(CH₃)₂, CH₂CH₂OCH₂CH₂—C₂H₅, 2-(1-methylpropoxy)ethyl,2-(2-methylpropoxy)ethyl, CH₂CH₂OC(CH₃)₃, CH₂CH₂O(CH₂)₃—C₂H₅,CH₂CH₂O(CH₂)₄—C₂H₅, 2-(OCH₃)propyl, 2-(OC₂H₅)propyl,2-(OCH₂—C₂H₅)propyl, 2-[OCH(CH₃)₂]propyl, 2-(OCH₂CH₂—C₂H₅)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-[OC(CH₃)₃]propyl, 3-(OCH₃)propyl, 3-(OC₂H₅)propyl,3-(OCH₂—C₂H₅)propyl, 3-[OCH(CH₃)₂]propyl, 3-(OCH₂CH₂—C₂H₅)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-[OC(CH₃)₃]propyl, 3-[O(CH₂)₃—C₂H₅]propyl, 3-[O(CH₂)₄—C₂H₅]propyl,2-(OCH₃)butyl, 2-(OC₂H₅)butyl, 2-(OCH₂—C₂H₅)butyl, 2-[OCH(CH₃)₂]butyl,2-(OCH₂CH₂—C₂H₅)butyl, 2-(1-methylpropoxy)butyl,2-(2-methylpropoxy)butyl, 2-[OC(CH₃)₃]butyl, 3-(OCH₃)butyl,3-(OC₂H₅)butyl, 3-(OCH₂—C₂H₅)butyl, 3-[OCH(CH₃)₂]butyl,3-(OCH₂CH₂—C₂H₅)butyl, 3-(1-methylpropoxy)butyl,3-(2-methylpropoxy)butyl, 3-[OC(CH₃)₃]butyl, 4-(OCH₃)butyl,4-(OC₂H₅)butyl, 4-(OCH₂—C₂H₅)butyl, 4-[OCH(CH₃)₂]butyl,4-(OCH₂CH₂—C₂H₅)butyl, 4-(1-methylpropoxy)butyl,4-(2-methylpropoxy)butyl, 4-[OC(CH₃)₃]butyl, 4-[O(CH₂)₃—C₂H₅]butyl,4-[O(CH₂)₄—C₂H₅]butyl, 5-(OCH₃)pentyl, 5-(OC₂H₅)pentyl,5-(OCH₂—C₂H₅)pentyl, 5-[OCH(CH₃)₂]pentyl, 5-(OCH₂CH₂—C₂H₅)pentyl,5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl,5-[OC(CH₃)₃]pentyl, 5-[O(CH₂)₃—C₂H₅]pentyl, 5-[O(CH₂)₄—C₂H₅]pentyl,6-(OCH₃)hexyl, 6-(OC₂H₅)hexyl, 6-(OCH₂—C₂H₅)hexyl, 6-[OCH(CH₃)₂]hexyl,6-(OCH₂CH₂—C₂H₅)hexyl, 6-(1-methylpropoxy)hexyl,6-(2-methylpropoxy)hexyl, 6-[OC(CH₃)₃]hexyl, 6-[O(CH₂)₃—C₂H₅]hexyl or6-[O(CH₂)₄—C₂H₅]hexyl, in particular CH₂OCH₃, CH(CH₃)OCH₃, CH₃CH₂OCH₃ orCH(CH₃)CH₂OCH₃;

hydroxycarbonyl-C₁-C₆-alkyl: eg. CH₂COOH, CH(CH₃)COOH, CH₂CH₂COOH,1-(COOH)prop-1-yl, 2-(COOH)prop-1-yl, 3-(COOH)prop-1-yl,1-(COOH)but-1-yl, 2-(COOH)but-1-yl, 3-(COOH)but-1-yl, 4-(COOH)but-1-yl1-(COOH)but-2-yl, 2-(COOH)but-2-yl, 3-(COOH)but-2-yl, 4-(COOH)but-2-yl,1-(CH₂COOH)eth-1-yl, 1-(CH₂COOH)-1-(CH₃)-eth-1-yl, 1-(CH₂COOH)prop-1-yl,5-(COOH)pent-1-yl or 6-(COOH)hex-1-yl;

(C₁-C₆-alkoxy)carbonyl: COOCH₃, COOC₂H₅, n-propoxycarbonyl, OCH(CH₃)₂,n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl,OC(CH₃)₃, n-pentoxycarbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexyloxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-C₂H₅-1-CH₃-propoxycarbonyl or 1-C₂H₅-2-CH₃-propoxycarbonyl, inparticular COOCH₃, COOC₂H₅ or COOC(CH₃)₃;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by(C₁-C₆-alkoxy)carbonyl as mentioned above, eg. CH₂COOCH₃, CH₂COOC₂H₅,CH₂COOCH₂—C₂H₅, CH₂COOCH(CH₃)₂, CH₂COOCH₂CH₂—C₂H₅,(1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl,CH₂COOC(CH₃)₃, CH₂COO(CH₂)₃—C₂H₅, CH₂COO(CH₂)₄—C₂H₅, CH(CH₃)COOCH₃,CH(CH₃)COOC₂H₅, CH₂CH₂COOCH₃, CH₂CH₂COOC₂H₅, CH₂CH₂COOCH₂—C₂H₅,CH₂CH₂COOCH(CH₃)₂, CH₂CH₂COOCH₂CH₂—C₂H₅,2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)ethyl,CH₂CH₂COOC(CH₃)₃, CH₂CH₂COO(CH₂)₃—C₂H₅, CH₂CH₂COO(CH₂)₄—C₂H₅,2-(COOCH₃)propyl, 2-(COOC₂H₅)propyl, 2-(COOCH₂—C₂H₅)propyl,2-[COOCH(CH₃)₂]propyl, 2-(COOCH₂CH₂—C₂H₅)propyl,2-(1-methylpropoxycarbonyl)propyl, 2-(2-methylpropoxycarbonyl)propyl,2-[COOC(CH₃)₃]propyl, 3-(COOCH₃)propyl, 3-(COOC₂H₅)propyl,3-(COOCH₂—C₂H₅)propyl, 3-[COOCH(CH₃)₂]propyl, 3-(COOCH₂CH₂—C₂H₅)propyl,3-(1-methylpropoxycarbonyl)propyl, 3-(2-methylpropoxycarbonyl)propyl,3-[COOC(CH₃)₃]propyl, 3-[COO(CH₂)₃—C₂H₅]propyl,3-[COO(CH₂)₄—C₂H₅]propyl, 2-(COOCH₃)butyl, 2-(COOC₂H₅)butyl,2-(COOCH₂—C₂H₅)butyl, 2-[COOCH(CH₃)₂]butyl, 2-(COOCH₂CH₂—C₂H₅)butyl,2-(1-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)butyl,2-[COOC(CH₃)₃]butyl, 3-(COOCH₃)butyl, 3-(COOC₂H₅)butyl,3-(COOCH₂—C₂H₅)butyl, 3-[COOCH(CH₃)₂]butyl, 3-(COOCH₂CH₂—C₂H₅)butyl,3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl,3-[COOC(CH₃)₃]butyl, 4-(COOCH₃)butyl, 4-(COOC₂H₅)butyl,4-(COOCH₂—C₂H₅)butyl, 4-[COOCH(CH₃)₂]butyl, 4-(COOCH₂CH₂—C₂H₅)butyl,4-(1-methylpropoxycarbonyl)butyl, 4-(2-methylpropoxycarbonyl)butyl,4-[COOC(CH₃)₃]butyl, 4-[COO(CH₂)₃—C₂H₅]butyl, 4-[COO(CH₂)₄—C₂H₅]butyl,5-(COOCH₃)pentyl, 5-(COOC₂H₅)pentyl, 5-(COOCH₂—C₂H₅)pentyl,5-[COOCH(CH₃)₂]pentyl, 5-(COOCH₂CH₂—C₂H₅)pentyl,5-(1-methylpropoxycarbonyl)pentyl, 5-(2-methylpropoxycarbonyl)pentyl,5-[COOC(CH₃)₃]pentyl, 5-[COO(CH₂)₃—C₂H₅]pentyl,5-[COO(CH₂)₄—C₂H₅]pentyl, 6-(COOCH₃)hexyl, 6-(COOC₂H₅)hexyl,6-(COOCH₂—C₂H₅)hexyl, 6-[COOCH(CH₃)₂]hexyl, 6-(COOCH₂CH₂—C₂H₅)hexyl,6-(1-methylpropoxycarbonyl)hexyl, 6-(2-methylpropoxycarbonyl)hexyl,6-[COOC(CH₃)₃]hexyl, 6-[COO(CH₂)₃—C₂H₅]hexyl or 6-[COO(CH₂)₄—C₂H₅]hexyl,in particular CH₂COOCH₃, CH₂COOCH(CH₃)₂ or CH(CH₃)COOCH₃;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substitutedby (C₁-C₆-alkoxy)carbonyl as mentioned above, eg. OCH₂COOCH₃,OCH₂COOC₂H₅, OCH₂COOCH₂—C₂H₅, OCH₂COOCH(CH₃)₂, OCH₂COOCH₂CH₂—C₂H₅,(1-methylpropoxycarbonyl)methoxy, (2-methylpropoxycarbonyl)methoxy,OCH₂COOC(CH₃)₃, OCH₂COO(CH₂)₃—C₂H₅, OCH₂COO(CH₂)₄—C₂H₅, OCH(CH₃)COOCH₃,OCH(CH₃)COOC₂H₅, OCH₂CH₂COOCH₃, OCH₂CH₂COOC₂H₅, OCH₂CH₂COOCH₂—C₂H₅,OCH₂CH₂COOCH(CH₃)₂, OCH₂CH₂COOCH₂CH₂—C₂H₅,2-(1-methylpropoxycarbonyl)ethoxy, 2-(2-methylpropoxycarbonyl)ethoxy,OCH₂CH₂COOC(CH₃)₃, OCH₂CH₂COO(CH₂)₃—C₂H₅, OCH₂CH₂COO(CH₂)₄—C₂H₅,2-(COOCH₃)propoxy, 2-(COOC₂H₅)propoxy, 2-(COOCH₂—C₂H₅)propoxy,2-[COOCH(CH₃)₂]propoxy, 2-(COOCH₂CH₂—C₂H₅)propoxy,2-(1-methylpropoxycarbonyl)propoxy, 2-(2-methylpropoxycarbonyl)propoxy,2-[COOC(CH₃)₃ _(])propoxy, 3-(COOCH₃)propoxy, 3-(COOC₂H₅)propoxy,3-(COOCH₂—C₂H₅)propoxy, 3-[COOCH(CH₃)₂]propoxy,3-(COOCH₂CH₂—C₂H₅)propoxy, 3-(1-methylpropoxycarbonyl)propoxy,3-(2-methylpropoxycarbonyl)propoxy, 3-[COOC(CH₃)₃]propoxy,3-[COO(CH₂)₃—C₂H₅]propoxy, 3-[COO(CH₂)₄—C₂H₅]propoxy, 2-(COOCH₃)butoxy,2-(COOC₂H₅)butoxy, 2-(COOCH₂—C₂H₅)butoxy, 2-[COOCH(CH₃)₂]butoxy,2-(COOCH₂CH₂—C₂H₅)butoxy, 2-(1-methylpropoxycarbonyl)butoxy,2-(2-methylpropoxycarbonyl)butoxy, 2-[COOC(CH₃)₃]butoxy,3-(COOCH₃)butoxy, 3-(COOC₂H₅)butoxy, 3-(COOCH₂—C₂H₅)butoxy,3-[COOCH(CH₃)₂]butoxy, 3-(COOCH₂CH₂—C₂H₅)butoxy,3-(1-methylpropoxycarbonyl)butoxy, 3-(2-methylpropoxycarbonyl)butoxy,3-[COOC(CH₃)₃]butoxy, 4-(COOCH₃)butoxy, 4-(COOC₂H₅)butoxy,4-(COOCH₂—C₂H₅)butoxy, 4-[COOCH(CH₃)₂]butoxy, 4-(COOCH₂CH₂—C₂H₅)butoxy,4-(1-methylpropoxycarbonyl)butoxy, 4-(2-methylpropoxycarbonyl)butoxy,4-[COOC(CH₃)₃]butoxy, 4-[COO(CH₂)₃—C₂H₅]butoxy,4-[COO(CH₂)₄—C₂H₅]butoxy, 5-(COOCH₃)pentoxy, 5-(COOC₂H₅)-pentoxy,5-(COOCH₂—C₂H₅)pentoxy, 5-[COOCH(CH₃)₂]pentoxy,5-(COOCH₂CH₂—C₂H₅)pentoxy, 5-(1-methylpropoxycarbonyl)pentoxy,5-(2-methylpropoxycarbonyl)pentoxy, 5-[COOC(CH₃)₃]pentoxy,5-[COO(CH₂)₃—C₂H₅]pentoxy, 5-[COO(CH₂)₄—C₂H₅]pentoxy,6-(COOCH₃)hexyloxy, 6-(COOC₂H₅)hexyloxy, 6-(COOCH₂—C₂H₅)hexyloxy,6-[COOCH(CH₃)₂]hexyloxy, 6-(COOCH₂CH₂—C₂H₅)hexyloxy,6-(1-methylpropoxycarbonyl)hexyloxy,6-(2-methylpropoxycarbonyl)hexyloxy, 6-[COOC(CH₃)₃]hexyloxy,6-[COO(CH₂)₃—C₂H₅]hexyloxy or 6-[COO(CH₂)₄—C₂H₅]hexyloxy, in particularOCH₂COOCH₃, OCH₂COOCH(CH₃)₂, OCH(CH₃)COOCH₃ or OCH₂CH₂COOCH₃;

C₁-C₆-alkylthio: eg. SCH₃, SC₂H₅, n-propylthio, SCH(CH₃)₂, n-butylthio,1-methylpropylthio, 2-methylpropylthio, SC(CH₃)₃, n-pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or1-ethyl-2-methylpropylthio, in particular SCH₃ or SC₂H₅;

C₁-C₆-haloalkylthio: a C₁-C₆-alkylthio radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCH(Cl)₂, SC(Cl)₃, SCHFCl,SCF(Cl)₂, SCF₂Cl, SCF₂Br, 2-fluoroethylthio, 2-chloroethylthio,2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, SC₂F₅, 2-fluoropropylthio,3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio,2,3-difluoropropylthio, 2,3-dichloropropylthio,3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio,2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio,1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio,1-(CH₂Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio,4-bromobutylthio, 5-fluoropentylthio, 5-chloropentylthio,5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexylthio or6-chlorohexylthio, in particular SCHF₂, SCF₃ or SC(Cl)₃;

C₁-C₆-alkylsulfinyl: eg. SOCH₃, SOC₂H₅, n-propylsulfinyl, SOCH(CH₃)₂,n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,SOC(CH₃)₃, n-pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, inparticular SOCH₃ or SOC₂H₅;

C₁-C₆-alkylsulfonyl: eg. SO₂CH₃, SO₂C₂H₅, n-propylsulfonyl, SO₂CH(CH₃)₂,n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl,SO₂C(CH₃)₃, n-pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, inparticular SO₂CH₃ or SO₂C₂H₅;

C₁-C₆-alkylaminosulfonyl: eg. H₃C—NHSO₂—, H₅C₂—NHSO₂—, n-propyl-NHSO₂—,(CH₃)₂CH—NHSO₂—, n-butyl-NHSO₂—, 1-methylpropyl-NHSO₂—,2-methylpropyl-NHSO₂—, (CH₃)₃C—NHSO₂—, n-pentyl-NHSO₂—,1-methylbutyl-NHSO₂—, 2-methylbutyl-NHSO₂—, 3-methylbutyl-NHSO₂—,2,2-dimethylpropyl-NHSO₂—, 1-ethylpropyl-NHSO₂—, n-hexyl-NHSO₂—,1,1-dimethylpropyl-NHSO₂—, 1,2-dimethylpropyl-NHSO₂—,1-methylpentyl-NHSO₂—, 2-methylpentyl-NHSO₂—, 3-methylpentyl-NHSO₂—,4-methylpentyl-NHSO₂—, 1,1-dimethylbutyl-NHSO₂—,1,2-dimethylbutyl-NHSO₂—, 1,3-dimethylbutyl-NHSO₂—,2,2-dimethylbutyl-NHSO₂—, 2,3-dimethylbutyl-NHSO₂—,3,3-dimethylbutyl-NHSO₂—, 1-ethylbutyl-NHSO₂—, 2-ethylbutyl-NHSO₂—,1,1,2-trimethylpropyl-NHSO₂—, 1,2,2-trimethylpropyl-NHSO₂—,1-ethyl-1-methylpropyl-NHSO₂— or 1-ethyl-2-methylpropyl-NHSO₂—, inparticular H₃C—NHSO₂— or H₅C₂—NHSO₂—;

di-(C₁-C₆-alkyl)aminosulfonyl: eg. (CH₃)₂N—SO₂—, (C₂H₅)₂N—SO₂—,N,N-dipropylamino-SO₂—, N,N-di(1-methylethyl)amino-SO₂—,N,N-dibutylamino-SO₂—, N,N-di(1-methylpropyl)amino-SO₂—,N,N-di(2-methylpropyl)amino-SO₂—, N,N-di(1,1-dimethylethyl)amino-SO₂—,N-ethyl-N-methylamino-SO₂—, N-methyl-N-propylamino-SO₂—,N-methyl-N-(1-methylethyl)amino-SO₂—, N-butyl-N-methylamino-SO₂—,N-methyl-N-(1-methylpropyl)amino-SO₂—,N-methyl-N-(2-methylpropyl)amino-SO₂—,N-(1,1-dimethylethyl)-N-methylamino-SO₂—, N-ethyl-N-propylamino-SO₂—,N-ethyl-N-(1-methylethyl)amino-SO₂—, N-butyl-N-ethylamino-SO₂—,N-ethyl-N-(1-methylpropyl)amino-SO₂—,N-ethyl-N-(2-methylpropyl)amino-SO₂—,N-ethyl-N-(1,1-dimethylethyl)amino-SO₂—,N-(1-methylethyl)-N-propylamino-SO₂—, N-butyl-N-propylamino-SO₂—,N-(1-methylpropyl)-N-propylamino-SO₂—,N-(2-methylpropyl)-N-propylamino-SO₂—,N-(1,1-dimethylethyl)-N-propylamino-SO₂—,N-butyl-N-(1-methylethyl)amino-SO₂—,N-(1-methylethyl)-N-(1-methylpropyl)amino-SO₂—,N-(1-methylethyl)-N-(2-methylpropyl)-amino-SO₂—,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino-SO₂—,N-butyl-N-(1-methylpropyl)amino-SO₂—,N-butyl-N-(2-methylpropyl)amino-SO₂—,N-butyl-N-(1,1-dimethylethyl)amino-SO₂—,N-(1-methylpropyl)-N-(2-methylpropyl)amino-SO₂—,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino-SO₂— orN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino-SO₂—, in particular(CH₃)₂N—SO₂—, (C₂H₅)₂N—SO₂— or N-ethyl-N-methylamino-SO₂—;

C₃-C₆-alkenyl: eg. prop-1-en-1-yl, allyl, 1-methylethenyl, n-buten-1-yl,n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl,n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl,1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl,4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethyl-prop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-2-en-1-yl or1-ethyl-2-methylprop-2-en-1-yl, in particular allyl;

C₃-C₆-alkynyl: eg. prop-1-yn-1-yl, propargyl, n-but-1-yn-1-yl,n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl,n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-3-yl,3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl,4-methyl-pent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particularpropargyl;

C₃-C₆-alkenyloxy: eg. prop-1-en-1-yloxy, allyloxy, 1-methylethenyloxy,n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy,n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy,n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy,n-hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy,2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy,4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy,2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy,4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy,2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy,4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy,2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy,4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy,1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy,1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy,1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy,1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy,2,3-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy,2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy,1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy,2-ethylbut-2-en-1-yloxy, 2-ethylbut-2-en-1-yloxy,2-ethylbut-3-en-1-yloxy, 1,1,2-trimethyl-prop-2-en-1-yloxy,1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methyl-prop-1-en-1-yloxy or1-ethyl-2-methylprop-2-en-1-yloxy, in particular allyloxy;

C₃-C₆-alkynyloxy: eg. prop-1-yn-1-yloxy, propargyloxy,n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy,n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy,n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy,n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methyl-but-1-yn-3-yloxy,3-methyl-but-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy,n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy,n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy,n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy,3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy,3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy,4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or4-methylpent-2-yn-5-yloxy, in particular propargyloxy.

With a view to the use of the substituted 2-phenylpyridines I asherbicides and/or compounds which have a desiccant/defoliant action, thevariables preferably have the following meanings, to be precise in eachcase alone or in combination:

n is zero;

R¹ is C₁-C₆-alkylsulfonyl, in particular SO₂CH₃;

R² is halogen, in particular chlorine;

R³ is hydrogen, fluorine or chlorine, especially preferably fluorine orchorine, in particular fluorine;

R⁴ is cyano or halogen, especially preferably cyano or chlorine, inparticular chlorine;

R⁵ is hydrogen, nitro, cyano, hydroxylamino, C₁-C₆-alkyl (in particularCH₃), C₁-C₆-haloalkyl (in particular halomethyl), —COCl, —CO—OR⁶,—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —O—(C₁-C₄-alkylene)—CO—OR⁶,—O—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —OR⁹, formyl,—CH═N—OR¹⁵ or —NH₂;

R⁶ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl orC₁-C₆-alkoxy-C₁-C₆-alkyl;

R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹⁵ is C₁-C₆-alkyl.

Very especially preferred are the compounds of the formula Ia({circumflex over (=)}I where n=zero; R¹=methylsulfonyl; R² andR⁴=chlorine; R³=fluorine), in particular the compounds of Table 1:

TABLE 1 Ia

No. R⁵ Ia.1 —H Ia.2 —F Ia.3 —Cl Ia.4 —Br Ia.5 —I Ia.6 —CN Ia.7 —CH₃ Ia.8—CH₂Cl Ia.9 —CHCl₂ Ia.10 —CCl₃ Ia.11 —CH₂Br Ia.12 —CHBr₂ Ia.13 —COClIa.14 —CO—OH Ia.15 —CO—OCH₃ Ia.16 —CO—OC₂H₅ Ia.17 —CO—OCH₂—C₂H₅ Ia.18—CO—OCH(CH₃)₂ Ia.19 —CO—OCH₂—CH₂—C₂H₅ Ia.20 —CO—OCH₂—CH(CH₃)₂ Ia.21—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.22 —CO—OCH₂—CCl₃ Ia.23 —CO—OCH₂—CF₃ Ia.24—CO—OCH₂—CH═CH₂ Ia.25 —CO—OCH₂—CH═CH—CH₃ Ia.26 —CO—OCH₂—CH₂—CH═CH₂ Ia.27—CO—OCH(CH₃)—CH═CH₂ Ia.28 —CO—OCH₂—CH₂—CH₂—CH═CH₂ Ia.29—CO—OCH₂—CH═C(CH₃)₂ Ia.30 —CO—OCH₂—C(CH₃)═CH—CH₃ Ia.31 —CO—OCH₂—C≡CHIa.32 —CO—OCH(CH₃)—C≡CH Ia.33 —CO—OCH₂—C≡C—CH₃ Ia.34 —CO—OCH₂—C≡C—C₂H₅Ia.35 —CO—O-cyclopropyl Ia.36 —CO—O-cyclobutyl Ia.37 —CO—O-cyclopentylIa.38 —CO—O-cyclohexyl Ia.39 —CO—OCH₂—CH₂—OCH₃ Ia.40 —CO—OCH₂—CH₂—OC₂H₅Ia.41 —CO—OCH₂—CH₂—OCH₂—CH₂—CH₃ Ia.42 —CO—OCH₂—CH₂—OCH(CH₃)₂ Ia.43—CO—O-(oxetan-3-yl) Ia.44 —CO—NH₂ Ia.45 —CO—NH—CH₃ Ia.46 —CO—N(CH₃)₂Ia.47 —CO—NH—CH₂—CO—OH Ia.48 —CO—NH—CH₂—CO—OCH₃ Ia.49—CO—NH—CH₂—CO—OC₂H₅ Ia.50 —CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.51—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.52 —CO—NH—CH(CH₃)—CO—OH Ia.53—CO—NH—CH(CH₃)—CO—OCH₃ Ia.54 —CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.55—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.56 —CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.57—CO—N(CH₃)—CH₂—CO—OH Ia.58 —CO—N(CH₃)—CH₂—CO—OCH₃ Ia.59—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.60 —CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.61—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.62 —CO—N(CH₃)—CH(CH₃)—CO—OH Ia.63—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.64 —CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.65—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.66—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.67 —CO-pyrrolidin-1-yl Ia.68—CO-piperidin-1-yl Ia.69 —CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.70—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.71 —CO—OCH₂—CO—OH Ia.72—CO—OCH₂—CO—OCH₃ Ia.73 —CO—OCH₂—CO—OC₂H₅ Ia.74 —CO—OCH₂—CO—OCH₂—C₂H₅Ia.75 —CO—OCH₂—CO—OCH(CH₃)₂ Ia.76 —CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.77—CO—OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.78 —CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.79—CO—OCH₂—CO—OC(CH₃)₃ Ia.80 —CO—OCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.81—CO—OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.82 —CO—OCH(CH₃)—CO—OH Ia.83—CO—OCH(CH₃)—CO—OCH₃ Ia.84 —CO—OCH(CH₃)—CO—OC₂H₅ Ia.85—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.86 —CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.87—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.88 —CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.89—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.90 —CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.91—CO—OCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.92—CO—OCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.93 —CO—OCH₂—CO—NH₂ Ia.94—CO—OCH₂—CO—NH—CH₃ Ia.95 —CO—OCH₂—CO—N(CH₃)₂ Ia.96—CO—OCH₂—CO—N(CH₃)—CH₂—CO—OH Ia.97 —CO—OCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.98—CO—OCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.99 —CO—OCH₂—CO-pyrrolidin-1-yl Ia.100—CO—OCH₂—CO-piperidin-1-yl Ia.101—CO—OCH₂—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.102—CO—OCH₂—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.103 —CO—OCH(CH₃)—CO—NH₂Ia.104 —CO—OCH(CH₃)—CO—NH—CH₃ Ia.105 —CO—OCH(CH₃)—CO—N(CH₃)₂ Ia.106—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.107—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.108—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.109—CO—OCH(CH₃)—CO-pyrrolidin-1-yl Ia.110 —CO—OCH(CH₃)—CO-piperidin-1-ylIa.111 —CO—OCH(CH₃)—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.112—CO—OCH(CH₃)—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.113 —OCH₂—CHO Ia.114—OCH₂—CO—CH₃ Ia.115 —OCH₂—CO—C₂H₅ Ia.116 —OCH₂—CO—CH(CH₃)₂ Ia.117—OCH₂—CO—CH₂—C₂H₅ Ia.118 —OCH₂—CO—CH₂—CH₂—C₂H₅ Ia.119—OCH₂—CO—CH₂—CH(CH₃)₂ Ia.120 —OCH₂—CO—CH(CH₃)—C₂H₅ Ia.121—OCH₂—CO—C(CH₃)₃ Ia.122 —OCH(CH₃)—CO—CH₃ Ia.123 —OCH(CH₃)—CO—C₂H₅ Ia.124—OCH(CH₃)—CO—CH₂—C₂H₅ Ia.125 —OCH(CH₃)—CO—CH(CH₃)₂ Ia.126—OCH(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.127 —OCH(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.128—OCH(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.129 —OCH(CH₃)—CO—C(CH₃)₃ Ia.130—OCH₂—CO—CH₂—Cl Ia.131 —OCH(CH₃)—CO—CH₂—Cl Ia.132 —OCH₂—CO—CH₂—CH═CH₂Ia.133 —OCH(CH₃)—CO—CH₂—CH═CH₂ Ia.134 —OCH₂—CO—CH₂—C≡CH Ia.135—OCH(CH₃)—CO—CH₂—C≡CH Ia.136 —OCH₂—CO-cyclopentyl Ia.137—OCH(CH₃)—CO-cyclohexyl Ia.138 —OCH₂—CO—CH₂—OCH₃ Ia.139—OCH(CH₃)—CO—CH₂—OCH₃ Ia.140 —OCH₂—CO—CH₂—OC₂H₅ Ia.141—OCH(CH₃)—CO—CH₂—OC₂H₅ Ia.142 —OCH₂—CO—CH₂—CH₂—OCH₃ Ia.143—OCH(CH₃)—CO—CH₂—CH₂—OCH₃ Ia.144 —OCH₂—CO—CH₂—CH₂—OC₂H₅ Ia.145—OCH(CH₃)—CO—CH₂—CH₂—OC₂H₅ Ia.146 —SCH₂—CHO Ia.147 —SCH₂—CO—CH₃ Ia.148—SCH₂—CO—C₂H₅ Ia.149 —SCH₂—CO—CH(CH₃)₂ Ia.150 —SCH₂—CO—CH₂—C₂H₅ Ia.151—SCH(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.152 —SCH(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.153—SCH(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.154 —SCH(CH₃)—CO—C(CH₃)₃ Ia.155—SCH₂—CO—CH₂—CH═CH₂ Ia.156 —SCH(CH₃)—CO—CH₂—CH═CH₂ Ia.157—SCH₂—CO—CH₂—CH≡CH Ia.158 —SCH(CH₃)—CO—CH₂—CH≡CH Ia.159—SCH₂—CO-cyclopentyl Ia.160 —SCH(CH₃)—CO-cyclopentyl Ia.161—SCH₂—CO-cyclohexyl Ia.162 —SCH(CH₃)—CO-cyclohexyl Ia.163—SCH₂—CO—CH₂—OCH₃ Ia.164 —SCH(CH₃)—CO—CH₂—OCH₃ Ia.165 —SCH₂—CO—CH₂—OC₂H₅Ia.166 —SCH(CH₃)—CO—CH₂—OC₂H₅ Ia.167 —SCH₂—CO—CH₂—CH₂—OCH₃ Ia.168—SCH(CH₃)—CO—CH₂—CH₂—OCH₃ Ia.169 —SCH₂—CO—CH₂—CH₂—OC₂H₅ Ia.170—SCH(CH₃)—CO—CH₂—CH₂—OC₂H₅ Ia.171 —OCH₂—CO—OH Ia.172 —OCH₂—CO—OCH₃Ia.173 —OCH₂—CO—OC₂H₅ Ia.174 —OCH₂—CO—OCH₂—C₂H₅ Ia.175—OCH₂—CO—OCH(CH₃)₂ Ia.176 —OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.177—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.178 —OCH₂—CO—OC(CH₃)₃ Ia.179—OCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.180 —OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.181—OCH(CH₃)—CO—OH Ia.182 —OCH(CH₃)—CO—OCH₃ Ia.183 —OCH(CH₃)—CO—OC₂H₅Ia.184 —OCH(CH₃)—CO—OCH₂—OC₂H₅ Ia.185 —OCH(CH₃)—CO—OCH(CH₃)₂ Ia.186—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.187 —OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.188—OCH(CH₃)—CO—OC(CH₃)₃ Ia.189 —OCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.190—OCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.191 —SCH₂—CO—OH Ia.192 —SCH₂—CO—OCH₃Ia.193 —SCH₂—CO—OC₂H₅ Ia.194 —SCH₂—CO—OCH₂—C₂H₅ Ia.195—SCH₂—CO—OCH(CH₃)₂ Ia.196 —SCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.197—SCH₂—CO—OCH₂—CH(CH₃)₂ Ia.198 —SCH₂—CO—OC(CH₃)₃ Ia.199—SCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.200 —SCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.201—SCH(CH₃)—CO—OH Ia.202 —SCH(CH₃)—CO—OCH₃ Ia.203 —SCH(CH₃)—CO—OC₂H₅Ia.204 —SCH(CH₃)—CO—OCH₂—C₂H₅ Ia.205 —SCH(CH₃)—CO—OCH(CH₃)₂ Ia.206—SCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.207 —SCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.208—SCH(CH₃)—CO—OC(CH₃)₃ Ia.209 —SCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.210—SCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.211 —OCH₂—CO—OCH₂—CO—OH Ia.212—OCH₂—CO—OCH₂—CO—OCH₃ Ia.213 —OCH₂—CO—OCH₂—CO—OC₂H₅ Ia.214—OCH₂—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.215 —OCH₂—CO—OCH₂—CO—OCH(CH₃)₂ Ia.216—OCH₂—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.217 —OCH₂—CO—OCH₂—CO—OCH₂—CH(CH₃)₂Ia.218 —OCH₂—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.219 —OCH₂—CO—OCH₂—CO—OC(CH₃)₃Ia.220 —OCH₂—CO—OCH(CH₃)—CO—OH Ia.221 —OCH₂—CO₂—CH(CH₃)—CO—OCH₃ Ia.222—OCH₂—CO—OCH(CH₃)—CO—OC₂H₅ Ia.223 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.224—OCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.225 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.226 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.227—OCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.228 —OCH₂—CO—OCH(CH₃)—CO—OC(CH₃)₃Ia.229 —OCH(CH₃)—CO—OCH₂—CO—OH Ia.230 —OCH(CH₃)—CO—OCH₂—CO—OCH₃ Ia.231—OCH(CH₃)—CO—OCH₂—CO—OC₂H₅ Ia.232 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.233—OCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)₂ Ia.234 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅Ia.235 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.236—OCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.237 —OCH(CH₃)—CO—OCH₂—CO—OC(CH₃)₃Ia.238 —OCH(CH₃)—CO—OCH(CH₃)—CO—OH Ia.239 —OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₃Ia.240 —OCH(CH₃)—CO—OCH(CH₃)—CO—OC₂H₅ Ia.241—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.242—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.243—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.244—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.245—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.246—OCH(CH₃)—CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.247 —SCH₂—CO—OCH₂—CO—OH Ia.248—SCH₂—CO—OCH₂—CO—OCH₃ Ia.249 —SCH₂—CO—OCH₂—CO—OC₂H₅ Ia.250—SCH₂—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.251 —SCH₂—CO—OCH₂—CO—OCH(CH₃)₂ Ia.252—SCH₂—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.253 —SCH₂—CO—OCH₂—CO—OCH₂—CH(CH₃)₂Ia.254 —SCH₂—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.255 —SCH₂—CO—OCH₂—CO—OC(CH₃)₃Ia.256 —SCH₂—CO—OCH(CH₃)—CO—OH Ia.257 —SCH₂—CO—OCH(CH₃)—CO—OCH₃ Ia.258—SCH₂—CO—OCH(CH₃)—CO—OC₂H₅ Ia.259 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.260—SCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.261 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.262 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.263—SCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.264 —SCH₂—CO—OCH(CH₃)—CO—OC(CH₃)₃Ia.265 —SCH(CH₃)—CO—OCH₂—CO—OH Ia.266 —SCH(CH₃)—CO—OCH₂—CO—OCH₃ Ia.267—SCH(CH₃)—CO—OCH₂—CO—OC₂H₅ Ia.268 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.269—SCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)₂ Ia.270 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅Ia.271 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.272—SCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.273 —SCH(CH₃)—CO—OCH₂—CO—OC(CH₃)₃Ia.274 —SCH(CH₃)—CO—OCH(CH₃)—CO—OH Ia.275 —SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₃Ia.276 —SCH(CH₃)—CO—OCH(CH₃)—CO—OC₂H₅ Ia.277—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.278—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.279—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.280—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.281—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.282—SCH(CH₃)—CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.283 —OCH₂—CO—NH₂ Ia.284—OCH₂—CO—NH—CH₃ Ia.285 —OCH₂—CO—N(CH₃)₂ Ia.286 —OCH₂—CO—NH—CH₂—CO—OHIa.287 —OCH₂—CO—NH—CH₂—CO—OCH₃ Ia.288 —OCH₂—CO—NH—CH₂—CO—OC₂H₅ Ia.289—OCH₂—CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.290 —OCH₂—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅Ia.291 —OCH₂—CO—NH—CH(CH₃)—CO—OH Ia.292 —OCH₂—CO—NH—CH(CH₃)—CO—OCH₃Ia.293 —OCH₂—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.294—OCH₂—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.295—OCH₂—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.296 —OCH₂—CO—N(CH₃)—CH₂—CO—OHIa.297 —OCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.298 —OCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅Ia.299 —OCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.300—OCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.301—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.302 —OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₃Ia.303 —OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.304—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.305—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.306 —OCH(CH₃)—CO—NH₂ Ia.307—OCH(CH₃)—CO—NH—CH₃ Ia.308 —OCH(CH₃)—CO—N(CH₃)₂ Ia.309—OCH(CH₃)—CO—NH—CH₂—CO—OH Ia.310 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.311—OCH(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.312 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₂—C₂H₅Ia.313 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.314—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OH Ia.315 —OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃Ia.316 —OCH(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.317—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.318—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.319—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.320 —OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃Ia.321 —OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.322—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.323—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.324—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.325—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.326—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.327—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.328—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.329 —SCH₂—CO—NH₂ Ia.330—SCH₂—CO—NH—CH₃ Ia.331 —SCH₂—CO—N(CH₃)₂ Ia.332 —SCH₂—CO—NH—CH₂—CO—OHIa.333 —SCH₂—CO—NH—CH₂—CO—OCH₃ Ia.334 —SCH₂—CO—NH—CH₂—CO—OC₂H₅ Ia.335—SCH₂—CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.336 —SCH₂—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅Ia.337 —SCH₂—CO—NH—CH(CH₃)—CO—OH Ia.338 —SCH₂—CO—NH—CH(CH₃)—CO—OCH₃Ia.339 —SCH₂—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.340—SCH₂—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.341—SCH₂—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.342 —SCH₂—CO—N(CH₃)—CH₂—CO—OHIa.343 —SCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.344 —SCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅Ia.345 —SCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.346—SCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.347—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.348 —SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₃Ia.349 —SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.350—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.351—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.352 —SCH(CH₃)—CO—NH₂ Ia.353—SCH(CH₃)—CO—NH—CH₃ Ia.354 —SCH(CH₃)—CO—N(CH₃)₂ Ia.355—SCH(CH₃)—CO—NH—CH₂—CO—OH Ia.356 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.357—SCH(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.358 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₂—C₂H₅Ia.359 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.360—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OH Ia.361 —SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃Ia.362 —SCH(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.363—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.364—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.365—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.366 —SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃Ia.367 —SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.368—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.369—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.370—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.371—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.372—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.373—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.374—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.375—OCH₂—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.376—OCH₂—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.377—OCH(CH₃)—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.378—OCH(CH₃)—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.379—SCH₂—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.380—SCH₂—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.381—SCH(CH₃)—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.382—SCH(CH₃)—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.383 —OH Ia.384 —OCH₃Ia.385 —OC₂H₅ Ia.386 —OCH₂—C₂H₅ Ia.387 —OCH(CH₃)₂ Ia.388 —OCH₂—CH₂—C₂H₅Ia.389 —OCH(CH₃)—C₂H₅ Ia.390 —OCH₂—CH(CH₃)₂ Ia.391 —OCH₂—CH₂—CH₂—C₂H₅Ia.392 —OCH₂—CH₂—CH(CH₃)—CH₃ Ia.393 —OCH₂—CF₃ Ia.394 —OCHF₂ Ia.395—OCH₂—CH═CH₂ Ia.396 —OCH₂—CH═CH—CH₃ Ia.397 —OCH₂—CH(CH₃)═CH₂ Ia.398—OCH(CH₃)—CH═CH₂ Ia.399 —OCH₂—CH═CH—C₂H₅ Ia.400 —OCH₂—CH₂—CH═CH—CH₃Ia.401 —OCH₂—CH₂—CH₂—CH═CH₂ Ia.402 —OCH₂—C≡CH Ia.403 —OCH(CH₃)—C≡CHIa.404 —OCH₂—C≡C—CH₃ Ia.405 —OCH₂—C≡C—C₂H₅ Ia.406 cyclopropyloxy Ia.407cyclobutyloxy Ia.408 cyclopentyloxy Ia.409 cyclohexyloxy Ia.410—OCH₂—CH₂—OCH₃ Ia.411 —OCH₂—CH₂—OC₂H₅ Ia.412 —OCH₂—CH₂—OCH₂—C₂H₅ Ia.413—OCH₂—CH₂—OCH(CH₃)₂ Ia.414 —SH Ia.415 —SCH₃ Ia.416 —SC₂H₅ Ia.417—SCH₂—C₂H₅ Ia.418 —SCH(CH₃)₂ Ia.419 —SCH₂—CH₂—C₂H₅ Ia.420 —SCH(CH₃)—C₂H₅Ia.421 —SCH₂—CH(CH₃)₂ Ia.422 —SCH₂—CH₂—CH₂—C₂H₅ Ia.423—SCH₂—CH₂—CH(CH₃)—CH₃ Ia.424 —SCH₂—CF₃ Ia.425 —SCHF₂ Ia.426 —SCH₂—CH═CH₂Ia.427 —SCH₂—CH═CH—CH₃ Ia.428 —SCH₂—CH(CH₃)═CH₂ Ia.429 —SCH(CH₃)—CH═CH₂Ia.430 —SCH₂—CH═CH—C₂H₅ Ia.431 —SCH₂—CH₂—CH═CH—CH₃ Ia.432—SCH₂—CH₂—CH₂—CH═CH₂ Ia.433 —SCH₂—C≡CH Ia.434 —SCH(CH₃)—C≡CH Ia.435—SCH₂—C≡C—CH₃ Ia.436 —SCH₂—C≡C—C₂H₅ Ia.437 cyclopropylthio Ia.438cyclobutylthio Ia.439 cyclopentylthio Ia.440 cyclohexylthio Ia.441—SCH₂—CH₂—OCH₃ Ia.442 —SCH₂—CH₂—OC₂H₅ Ia.443 —SCH₂—CH₂—OCH₂—C₂H₅ Ia.444—SCH₂—CH₂—OCH(CH₃)₂ Ia.445 —CH═CH₂—CO—OH Ia.446 —CH═CH₂—CO—OCH₃ Ia.447—CH═CH₂—CO—OC₂H₅ Ia.448 —CH═CH₂—CO—OCH₂—C₂H₅ Ia.449—CH═CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.450 —CH═CH(Cl)—CO—OH Ia.451—CH═CH(Cl)—CO—OCH₃ Ia.452 —CH═CH(Cl)—CO—OC₂H₅ Ia.453—CH═CH(Cl)—CO—OCH₂—C₂H₅ Ia.454 —CH═CH(Cl)—CO—OCH₂—CH₂—C₂H₅ Ia.455—CH═CH(CH₃)—CO—OH Ia.456 —CH═CH(CH₃)—CO—OCH₃ Ia.457 —CH═CH(CH₃)—CO—OC₂H₅Ia.458 —CH═CH(CH₃)—CO—OCH₂—C₂H₅ Ia.459 —CH═CH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.460 —CH═CH—CO—NH₂ Ia.461 —CH═CH—CO—NH—CH₃ Ia.462 —CH═CH—CO—N(CH₃)₂Ia.463 —CH═CH—CO—NH—CH₂—CO—OH Ia.464 —CH═CH—CO—NH—CH₂—CO—OCH₃ Ia.465—CH═CH—CO—NH—CH₂—CO—OC₂H₅ Ia.466 —CH═CH—CO—NH—CH(CH₃)—CO—OH Ia.467—CH═CH—CO—NH—CH(CH₃)—CO—OCH₃ Ia.468 —CH═CH—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.469—CH═CH—CO—N(CH₃)—CH₂—CO—OH Ia.470 —CH═CH—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.471—CH═CH—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.472 —CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OHIa.473 —CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.474—CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.475 —CH═C(Cl)—CO—NH—CH(CH₃)—CO—OHIa.476 —CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.477—CH═C(Cl)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.478 —CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OHIa.479 —CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.480—CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.481—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.482—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.483—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.484—CH═C(Cl)—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.485—CH═C(Cl)—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.486 —CHO Ia.487 —CO—CH₃Ia.488 —CO—C₂H₅ Ia.489 —CO—CH₂—C₂H₅ Ia.490 —CO—CH(CH₃)₂ Ia.491—CO—CH₂—CH₂—C₂H₅ Ia.492 —CO—CH₂—CH(CH₃)—CH₃ Ia.493 —CO—CH(CH₃)—C₂H₅Ia.494 —CO—CH₂—Cl Ia.495 —CO—CH₂—Br Ia.496 —CO—CHCl₂ Ia.497 —CO—CHBr₂Ia.498 —CO—CCl₃ Ia.499 —CO—CF₃ Ia.500—CH═CH—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.501—CH═CH—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.502 —CH═C(CH₃)—CO—NH₂ Ia.503—CH═C(CH₃)—CO—NH—CH₃ Ia.504 —CH═C(CH₃)—CO—N(CH₃)₂ Ia.505—CH═C(CH₃)—CO—NH—CH₂—CO—OH Ia.506 —CH═C(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.507—CH═C(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.508 —CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OHIa.509 —CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.510—CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.511 —CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OHIa.512 —CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.513—CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.514—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.515—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.516—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.517—CH═C(CH₃)—CO-[2-(COOCH₃)-pyrrolidin-1-yl] Ia.518—CH═C(CH₃)—CO-[2-(COOC₂H₅)-pyrrolidin-1-yl] Ia.519 —CH═C(Cl)—CO—NH₂Ia.520 —CH—C(Cl)—CO—NH—CH₃ Ia.521 —CH═C(Cl)—CO—N(CH₃)₂ Ia.522—CH═C(Cl)—CO—NH—CH₂—CO—OH Ia.523 —CH═C(Cl)—CO—NH—CH₂—CO—OCH₃ Ia.524—CH═C(Cl)—CO—NH—CH₂—CO—OC₂H₅ Ia.525 —CO—CH₂—CH═CH₂ Ia.526—CO—CH₂—CH═CH—CH₃ Ia.527 —CO—CH₂—CH₂—CH═CH₂ Ia.528 —CO—CH₂—C≡CH Ia.529—CO—CH(CH₃)—C≡CH Ia.530 —CO—CH₂—C≡C—CH₃ Ia.531 cyclopropylcarbonylIa.532 cyclobutylcarbonyl Ia.533 cyclopentylcarbonyl Ia.534cyclohexylcarbonyl Ia.535 —CO—CH₂—OCH₃ Ia.536 —CO—CH₂—OC₂H₅ Ia.537—CO—CH₂—CH₂—OCH₃ Ia.538 —CO—CH₂—CH₂—OC₂H₅ Ia.539 1,3-dioxolan-2-ylIa.540 4-(CH₃)-1,3-dioxolan-2-yl Ia.541 4,5-(CH₃)₂-1,3-dioxolan-2-ylIa.542 4,4-(CH₃)₂-1,3-dioxolan-2-yl Ia.5434,4,5-(CH₃)₃-1,3-dioxolan-2-yl Ia.544 4,4,5,5-(CH₃)₄-1,3-dioxolan-2-ylIa.545 4-(COOCH₃)-1,3-dioxolan-2-yl Ia.546 4-(COOC₂H₅)-1,3-dioxolan-2-ylIa.547 4-(COOCH₂C₂H₅)-1,3-dioxolan-2-yl Ia.5484-[COOCH(CH₃)₂]-1,3-dioxolan-2-yl Ia.5494-(COOCH₂CH₂—C₂H₅)-1,3-dioxolan-2-yl Ia.5504-[COOCH₂CH(CH₃)₂]-1,3-dioxolan-2-yl Ia.5514-[COOCH(CH₃)C₂H₅]-1,3-dioxolan-2-yl Ia.5524-[COOC(CH₃)₃]-1,3-dioxolan-2-yl Ia.553 4,5-(COOCH₃)₂-1,3-dioxolan-2-ylIa.554 4,5-(COOC₂H₅)₂-1,3-dioxolan-2-yl Ia.555

Ia.556 1,3-Dithiolan-2-yl Ia.557 4-(CH₃)-1,3-dithiolan-2-yl Ia.5584,5-(CH₃)₂-1,3-dithiolan-2-yl Ia.559 4,4-(CH₃)₂-1,3-dithiolan-2-ylIa.560 4-(COOCH₃)-1,3-dithiolan-2-yl Ia.5614-(COOC₂H₅)-1,3-dithiolan-2-yl Ia.562 4-(COOCH₂C₂H₅)-1,3-dithiolan-2-ylIa.563 4-[COOCH(CH₃)₂]-1,3-dithiolan-2-yl Ia.5644-(COOCH₂CH₂C₂H₅)-1,3-dithiolan-2-yl Ia.5654-[COOCH₂CH(CH₃)₂]-1,3-dithiolan-2-yl Ia.5664-[COOCH(CH₃)C₂H₅]-1,3-dithiolan-2-yl Ia.5674-[COOC(CH₃)₃]-1,3-dithiolan-2-yl Ia.5684,5-(COOCH₃)₂-1,3-dithiolan-2-yl Ia.5694,5-(COOC₂H₅)₂-1,3-dithiolan-2-yl Ia.570 —CH═N—OH Ia.571 —CH═N—OCH₃Ia.572 —CH═N—OC₂H₅ Ia.573 —CH═N—OCH₂—C₂H₅ Ia.574 —CH═N—OCH(CH₃)₂ Ia.575—CH═N—OCH₂—CH₂—C₂H₅ Ia.576 —CH═N—OCH₂—CH(CH₃)₂ Ia.577—CH═N—OCH(CH₃)—C₂H₅ Ia.578 —CH═N—OC(CH₃)₃ Ia.579 —CH═N—OCH₂—CH₂—CH₂—C₂H₅Ia.580 —CH═N—OCH₂—CH₂—CH(CH₃)₂ Ia.581 —CH═N—OCH₂—CO—OCH₃ Ia.582—CH═N—OCH₂—CO—OC₂H₅ Ia.583 —CH═N—OCH₂—CO—OCH₂—C₂H₅ Ia.584—CH═N—OCH(CH₃)—CO—OCH₃ Ia.585 —CH═N—OCH(CH₃)—CO—OC₂H₅ Ia.586—CH═N—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.587 —CH(OCH₃)₂ Ia.588 —CH(OC₂H₅)₂ Ia.589—CH(OCH₂—C₂H₅)₂ Ia.590 —CH(OCH₂—CH₂—C₂H₅)₂ Ia.591 —NO₂ Ia.592 —NH—OHIa.593 —NH₂ Ia.594 —NH—CH₃ Ia.595 —N(CH₃)₂ Ia.596 —NH—CH₂—CO—OCH₃ Ia.597—NH—CH₂—CO—OC₂H₅ Ia.598 —NH—CH₂—CO—OCH₂—C₂H₅ Ia.599—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.600 —NH—CH(CH₃)—CO—OCH₃ Ia.601—NH—CH(CH₃)—CO—OC₂H₅ Ia.602 —NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.603—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.604 —N(CH₃)—CH₂—CO—OCH₃ Ia.605—N(CH₃)—CH₂—CO—OC₂H₅ Ia.606 —N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.607—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.608 —N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.609—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.610 —N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.611—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.612 —NH—SO₂—CH₃ Ia.613 —NH—SO₂—C₂H₅Ia.614 —NH—SO₂—CH₂—C₂H₅ Ia.615 —NH—SO₂—CH(CH₃)₂ Ia.616—NH—SO₂—CH₂—CH₂—C₂H₅ Ia.617 —NH—SO₂—CH₂—CH(CH₃)₂ Ia.618—NH—SO₂—CH(CH₃)—C₂H₅ Ia.619 —N(CH₃)—SO₂—CH₃ Ia.620 —N(CH₃)—SO₂—C₂H₅Ia.621 —N(CH₃)—SO₂—CH₂—C₂H₅ Ia.622 —N(CH₃)—SO₂—CH(CH₃)₂ Ia.623—N(CH₃)—SO₂—CH₂—CH₂—C₂H₅ Ia.624 —N(CH₃)—SO₂—CH₂—CH(CH₃)₂ Ia.625—NH—CO—CH₃ Ia.626 —NH—CO—C₂H₅ Ia.627 —NH—CO—CH₂—C₂H₅ Ia.628—NH—CO—CH(CH₃)₂ Ia.629 —NH—CO—CH₂—CH₂—C₂H₅ Ia.630 —NH—CO—CH₂—CH(CH₃)₂Ia.631 —NH—CO—CH(CH₃)—C₂H₅ Ia.632 —NH—CO—C(CH₃)₃ Ia.633 —N(CH₃)—CO—CH₃Ia.634 —N(CH₃)—CO—C₂H₅ Ia.635 —N(CH₃)—CO—CH₂—C₂H₅ Ia.636—N(CH₃)—CO—CH(CH₃)₂ Ia.637 —N(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.638—N(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.639 —N(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.640—N(CH₃)—CO—C(CH₃)₃ Ia.641 —SO₂—Cl Ia.642 —SO₂—OH Ia.643 —SO₂—NH₂ Ia.644—SO₂—NH—CH₃ Ia.645 —SO₂—N(CH₃)₂ Ia.646 —SO₂—NH—CH₂—CO—OCH₃ Ia.647—SO₂—NH—CH₂—CO—OC₂H₅ Ia.648 —SO₂—NH—CH(CH₃)—CO—OCH₃ Ia.649—SO₂—NH—CH(CH₃)—CO—OC₂H₅ Ia.650 —SO₂—N(CH₃)—CH₂—CO—OCH₃ Ia.651—SO₂—N(CH₃)—CH₂—CO—OC₂H₅ Ia.652 —SO₂—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.653—SO₂—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.654 1,3-dioxan-2-yl Ia.6554-(CH₃)-1,3-dioxan-2-yl Ia.656 5-(CH₃)-1,3-dioxan-2-yl Ia.6575,5-(CH₃)₂-1,3-dioxan-2-yl Ia.658

Ia.659 1,3-dithian-2-yl Ia.660 4-(CH₃)-dithian-2-yl Ia.6615-(CH₃)-dithian-2-yl Ia.662 5,5-(CH₃)₂-dithian-2-yl

Other very especially preferred substituted 2-phenylpyridines are thoseof the formulae Ib, Ic, Id, Ie and If, in particular

the compounds Ib.1 to Ib.662, which differ from the correspondingcompounds Ia.1 to Ia.662 only in that R³ is chlorine:

the compounds Ic.1 to Ic.662, which differ from the correspondingcompounds Ia.1 to Ia.662 only in that R³ is hydrogen:

the compounds Id.1 to Id.662, which differ from the correspondingcompounds Ia.1 to Ia.662 only in that R³ is cyano:

the compounds Ie.1 to Ie.662, which differ from the correspondingcompounds Ia.1 to Ia.662 only in that R³ is chlorine and R⁴ is cyano:

the compounds If.1 to If.662, which differ from the correspondingcompounds Ia.1 to Ia.662 only in that R³ is hydrogen and R⁴ is cyano:

The substituted 2-phenylpyridines of the formula I are accessible invarious ways, for example by one of the following processes:

Process A

Oxidation of substituted 2-phenylpyridines of the formula I where n iszero and R¹ and R⁵ do not contain oxidizable sulfur, in a manner knownper se {cf. for example, A. Albini & S. Pietra, Heterocyclic N-Oxides,CRC-Press Inc., Boca Raton, USA 1991; H. S. Mosher et al., Org. Synth.Coll. Vol. IV 1963, page 828; E. C. Taylor et al., Org. Synth. Coll.Vol. IV 1963, page 704; T. W. Bell et. al., Org. Synth. 69 (1990), page226}:

Among the oxidants conventionally used for oxidizing the pyridine ring,reference may be made by way of example to peracetic acid,trifluoroperacetic acid, perbenzoic acid, m-chloroperbenzoic acid,monopermaleic acid, magnesium monoperphthalate, sodium perborate, Oxone®(contains peroxydisulfate), pertungstic acid and hydrogen peroxide.

Examples of suitable solvents are water, sulfuric acid, carboxylic acidssuch as acetic acid and trifluoroacetic acid, and also halogenatedhydrocarbons such as dichloromethane and chloroform.

The oxidation is normally successfully carried out at from 0° C. to theboiling point of the reaction mixture.

The oxidant is normally employed in at least equimolar amounts based onthe starting compound. In general, an excess of oxidant has proved to beespecially advantageous.

Process B

Oxidation of substituted 2-phenylpyridines of the formula I where R¹ isC₁-C₆-alkylthio or C₁-C₆-alkylsulfinyl and the substituent R⁵ does notcontain oxidizable sulfur, in a manner known per se {cf., for example,C. S. Giam et al., Org. Prep. Proced. Int. 13(2) (1981), p. 137; S. G.Woods et al., J. Heterocycl. Chem. 21 (1984), 97-101; S. G. Woods, U.S.Pat. No. 4,616,087; N. Finch et al., J. Med. Chem. 21(12) (1978),1269-1274; H. Ban-Oganowska, Pd. J. Chem. 67(9) (1993), 1609-1613; A. D.Dunn & R. Norrie, J. Prakt. Chem./Chem.-Ztg. 335 (1993), 269-272}:

As regards suitable solvents and reaction temperatures, reference may bemade to the information given for Process A). Oxidants which aresuitable in addition to those mentioned for Process A) are also alkalimetal hypohalites such as sodium hypochlorite and potassiumhypochlorite.

To prepare products of value I where R¹=alkylsulfinyl, it is recommendedto employ not more than approx. 1.1 equivalents of the oxidant. Toprepare I where R¹=alkylsulfonyl, it is necessary to employ at least oneequivalent or at least two equivalents of the oxidant, depending onwhether the starting material is a corresponding compound I whereR¹=alkylthio or a corresponding compound I where R¹=alkylsulfinyl.

Process C

Transition-metal-catalyzed cross-coupling reaction of 2-halopyridines II(Hal=chlorine or bromine) with organometallic compounds of the formulaIII in a manner known per se {cf., for example, WO 95/02580 and theliterature cited therein on pages 21 and 22}:

M¹ is B(OH)₂, Mg—Cl, Mg—Br, Mg—I, Zn—Cl, Zn—Br, Zn—I, lithium, copper ortin-tri(C₁-C₄-alkyl), preferably B(OH)₂, Mg—Cl, Mg—Br, Mg—I, Zn—Cl,Zn—Br or Zn—I.

Alternatively, it is also possible to employ the boron oxines IV insteadof the boronic acids III {M¹=B(OH)₂}.

Suitable catalysts are, in particular, palladium catalysts such astetrakis(triphenylphosphine)palladium(O),bis(triphenylphosphine)palladium(II) chloride,1,4-bis(diphenylphosphino)-butanepalladium(II) chloride,1,2-bis(diphenylphosphino)ethanepalladium(II) chloride, palladium(II)acetate+triphenylphosphine, palladium(II) acetate+tri(o-tolyl)phosphineor palladium on active charcoal, and nickel catalysts such asbis(triphenylphosphine)nickel(II) chloride,1,3-bis(diphenylphosphino)propanenickel(II) chloride ornickel(II)acetylacetonate.

Process D

Reduction of 5-nitro-2-phenylpyridines of the formula V to give5-amino-2-phenylpyridines VI, diazotization of the amino group andreaction of the diazonium salts with a symmetric aliphatic disulfide ofthe formula VII in a manner known per se:

Reactions of this type are generally known, for example from thefollowing publications:

Reduction of nitropyridines with hydrogen: F. Janssens et al., J. Med.Chem. 28(12) (1985), p. 1943;

Reduction of nitropyridines with iron: B. A. Fox et al., Org. Synth. 44(1964), p. 34;

Reduction of nitropyridines with tin(II) chloride: L. A. Perez-Medina etal., J. Am. Chem. Soc. 69 (1947), p. 2574;

Reduction of nitropyridines with hydrazine: G. J. Clark et al., Aust. J.Chem. 34 (1981), p. 927;

Reduction of nitropyridines with tin: K. Wojciechowski et al., Synthesis8 (1986), 651-653;

Reduction of nitropyridines with low-valency titanium compounds: M.Malinowski, B. Soc. Chim. Belg. 97(1) (1988), 51-53;

Reduction of nitropyridines with baker's yeast: M. Takeshita et al.,Heterocycles 31(12) (1990), 2201-2204;

Reduction of nitropyridines with zinc: K. Goerlitzer et al., Arch.Pharm. 324(10) (1991), 785-796;

Reduction of nitropyridines with sodium dithionite: F. G. Fischer etal., Ann. Chem. 651 (1962), p. 49;

Diazotization of aminopyridines with isoamyl nitrite and reaction of thediazonium salts with dimethyl disulfide or diphenyl disulfide: C. S.Giam et al., J. Chem. Soc., Chem. Commun. 16 (1980), p. 756; T.Yasumitsu et al., J. Org. Chem. 46, 3564-3567 (1981).

2-(4-Chloro-3-methoxyphenyl)-5-nitropyridine,2-(4-chloro-3-methoxyphenyl)-3-chloro-5-nitropyridine,5-amino-2-(4-chloro-3-methoxyphenyl)pyridine and5-amino-2-(4-chloro-3-methoxyphenyl)-3-chloropyridine have already beendisclosed in WO 95/02580. Apart from these compounds, the5-nitro-2-phenylpyridines V and the 5-amino-2-phenylpyridines VI arenovel. The preparation of V is expediently carried out by a methodsimilar to process C) by a transition-metal-catalyzed cross-couplingreaction of 2-halo-5-nitropyridines of the formula VIII (Hal=chlorine orbromine) with organometallic compounds of the formula IX {cf., forexample, M. B. Mitchell et al., Tetrahedron Lett. 32 (1991), 2273-2276}:

M² is B(OH)₂, Zn—Cl, Zn—Br, Zn—I, copper or tin-tri(C₁-C₄-alkyl).

The catalysts given for process C) are also suitable in this context.

Process E

Diazotization of 5-amino-2-phenylpyridines of the formula VI andreaction of the diazonium salts with SO₂ in the presence of copper(II)chloride {cf., for example, U.S. Pat. No. 4,784,684 and Gilbert inSynthesis 1969, p. 6}:

The reaction of I (R¹=SO₂Cl) with ammonia, primary or secondary aminesleads to the corresponding compounds I where R¹=H₂N—SO₂, alkyl-NH—SO₂ or(alkyl)₂N—SO₂ {cf., for example, C. Naegeli et al., Helv. Chim. Acta 25(1942), 1485; M. Yasuhiro et al., J. Med. Chem. 23 (1980), 1376-1380; J.F. Liegeois et al., Helv. Chim. Acta 74 (1991), 8, 1764-1772 and P. DeTullio et al., Tetrahedron 51 (1995), 11, 3221-3234}:

Moreover, the substituted 2-phenylpyridines I where R¹=chlorosulfonylcan also be hydrolyzed to give the corresponding compounds I whereR¹=hydroxysulfonyl.

The substituted 2-phenylpyridines I can normally be prepared by one ofthe abovementioned synthesis processes. However, it may be moreexpedient for economic or process engineering reasons to prepare somecompounds I from similar 2-phenylpyridines, which, however, differ inthe meaning of one radical.

The compounds of the formula IIa

are novel. 2-Chloro-5-methylthiopyridine is known, for example, from J.Med. Chem. 16 (1973), 319-327. As regards 2-chloro-5-methylsulfinyl- and2-chloro-5-methylsulfonylpyridine, cf. J. Med. Chem. 29 (1986), 427-433;as regards 2-bromo-5-tert-butylthiopyridine, reference may be made toBull. Soc. Chim. Belg. 95 (1986), 1009-1020.

In general, the preparation of the 2-halopyridines II can be carried outfor example by diazotizing the corresponding 5-aminopyridines X¹⁾—preferably with a nitrous ester such as tert-butyl nitrite andisopentyl nitrite—and subsequently reacting the diazonium salt with asymmetric aliphatic disulfide VII {cf., for example, J. Chem. Soc.,Chem. Commun. 1980, p. 756-757}:

¹⁾ Re the preparation thereof, see J. Med. Chem. 16, 319-327 (1973)

The diazotization can be also carried out in the presence of thedisulfide VII.

The process is preferably carried out in an anhydrous system, forexample in glacial acetic acid which contains hydrogen chloride, indioxane, absolute ethanol, tetrahydrofuran, acetonitrile, or in acetone.

The reaction temperature is normally at from (−30) to 80° C.

The components in the diazotization reaction are usually employed in anapproximately stoichiometric ratio, but an excess of one of thecomponents may also be advantageous, for example with a view to ascomplete a reaction as possible of the other components. It is preferredto use an excess of nitrite, up to approximately twice the molar amount,based on the amount of X.

The disulfide VII is expediently employed in approximately equimolaramounts or in an excess, based on the diazonium salt. In general, alarge excess of disulfide VII (up to approximately 5 times the molaramount), based on the amount of diazonium salt, has proved to beespecially advantageous.

The 2-halopyridines II where R¹=C₁-C₆-alkylthio can subsequently beoxidized to give the corresponding compounds whereR¹=C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, as described underprocess B) for the compounds I where R¹=C₁-C₆-alkylthio.

Unless otherwise specified, all the above-described processes areexpediently carried out under atmospheric pressure or under the inherentpressure of the reaction mixture in question.

As a rule, the reaction mixtures are worked up by methods known per se,for example diluting the reaction solution with water and subsequentlyisolating the product by means of filtration, crystallization or solventextraction, or removing the solvent, partitioning the residue in amixture of water and a suitable organic solvent and working up theorganic phase to give the product.

The substituted 2-phenylpyridines I can be obtained upon preparation inthe form of isomer mixtures, but, if desired, these can be separatedinto the essentially pure isomers by the methods conventionally used forthis purpose, such as crystallization or chromatography, also on anoptically active absorbent. Pure, optically active isomers can beprepared advantageously from corresponding optically active startingmaterials.

Agriculturally useful salts of the compounds I can be formed by means ofa reaction with a base of the corresponding cation, preferably an alkalimetal hydroxide or alkali metal hydride.

Salts of I whose metal ion is not an alkali metal ion can also beprepared in a customary manner by double decomposition of thecorresponding alkali metal salt, and also ammonium, phosphonium,sulfonium and sulfoxonium salts by means of ammonia, phosphoniumhydroxide, sulfonium hydroxide or sulfoxonium hydroxide.

The compounds I and their agriculturally useful salts, not only asisomer mixtures but also in the form of the pure isomers, are suitableas herbicides. The herbicidal compositions comprising I effect very goodcontrol of vegetation on non-crop areas, especially at high rates ofapplication. In crops such as wheat, rice, maize, soybeans and cotton,they are active against broad-leaved weeds and grass weeds withoutinflicting any appreciable damage on the crop plants. This effect occursmainly at low rates of application.

Depending on the application method in question, the compounds I orherbicidal compositions comprising them can be employed in a furtheramount of crop plants for eliminating undesirable plants. Suitable cropsare, for example, the following: Allium cepa, Ananas comosus, Arachishypogaea, Asparagus officinalis, Beta vulgaris subsp. altissima, Betavulgaris subsp. rapa, Brassica napus var. napus, Brassica napus var.napobrassica, Brassica rapa var. silvestris, Camellia sinensis,Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrussinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumissativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragariavesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypiumherbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis,Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lensculinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec.,Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolusvulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunuspersica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in crops which toleratethe action of herbicides as a result of breeding, including geneticengineering methods.

Moreover, the substituted 2-phenylpyridines I are also suitable for thedesiccation and/or defoliation of plants.

As desiccants, they are suitable, in particular, for desiccating theaerial parts of crop plants such as potatoes, oilseed rape, sunflowersand soybeans. This allows completely mechanical harvesting of theseimportant crop plants.

Also of economic interest is facilitating harvesting, which is madepossible in citrus fruit, olives or other species and varieties ofpomaceous fruit, stone fruit and nuts by concentrating, over a period oftime, the adhesions or a reduced adhesion to the tree. The samemechanism, ie. promotion of the formation of abscission between fruit orleaf and shoot of the plants is also essential for readily controllabledefoliation of crop plants, in particular cotton.

Moreover, the shortened period of time within which the individualcotton plants mature results in a better fiber quality after harvesting.

The compounds I or the compositions comprising them can be used, forexample, in the form of directly sprayable aqueous solutions, powders,suspensions, also highly concentrated aqueous, oily or other suspensionsor dispersions, emulsions, oil dispersions, pastes, dusts, materials forspreading or granules by means of spraying, atomizing, dusting,spreading or pouring. The use forms depend on the intended aims; in anycase, they should guarantee the finest possible distribution of theactive ingredients according to the invention.

Suitable inert auxiliaries are essential:

Mineral oil fractions of medium to high boiling point such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, eg.paraffins, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstances, as such or dissolved in an oil or solvent, can behomogenized in water by means of wetting agent tackifier, dispersant oremulsifier. Alternatively, it is possible to prepare concentratescomposed of active substance, wetting agent, tackifier, dispersant oremulsifier and, if appropriate, solvent or oils, and these concentratesare suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, eg.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid and offatty acids, of alkyl- and alkylarylsulfonates, of alkyl sulfates,lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfatedhexa-, hepta- and octadecanols and of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenyl ethers,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycolethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active substances together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, andproducts of vegetable origin such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders or other solid carriers.

The concentrations of the active ingredients I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight, of at least one active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

The formulation examples which follow illustrate the preparation of suchproducts:

I. 20 parts by weight of the compound No. Ia.181 are dissolved in amixture composed of 80 parts by weight of alkylated benzene, 10 parts byweight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calciumdodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol ofethylene oxide and 1 mol of castor oil. Pouring the solution into100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive ingredient.

II. 20 parts by weight of the compound No. Ia.384 are dissolved in amixture composed of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of theadduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active ingredient.

III. 20 parts by weight of the active ingredient No. Ia.402 aredissolved in a mixture composed of 25 parts by weight of cyclohexanone,65 parts by weight of mineral oil fraction of boiling point 210 to 280°C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide and1 mol of castor oil. Pouring the solution into 100,000 parts by weightof water and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the active ingredient No. 2 are mixedthoroughly with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activeingredient.

V. 3 parts by weight of the active ingredient No. 3 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the active ingredient No. 7 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the active ingredient No. 10 is dissolved in amixture composed of 70 parts by weight of cyclohexanone, 20 parts byweight of ethoxylated isooctylphenol and 10 parts by weight ofethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the active ingredient No. 13 is dissolved in amixture composed of 80 parts by weight of cyclohexanone and 20 parts byweight of Wettol® EM 31 (=non-ionic emulsifier based on ethoxylatedcastor oil; BASF AG). This gives a stable emulsion concentrate.

The active ingredients I or the herbicidal compositions can be appliedpre- or post-emergence. If the active ingredients are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into as little contactas possible, if any, with the leaves of the sensitive crop plants whilereaching the leaves of undesirable plants which grow underneath, or thebare soil (post-directed, lay-by).

Depending on the intended aim of the control measures, the season, thetarget plants and the growth stage, the rates of application of activeingredient I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha ofactive substance (a.s.).

To widen the spectrum of action and to achieve synergistic effects, thesubstituted 2-phenylpyridines I can be mixed with a large number ofrepresentatives of other groups of active ingredients which have aherbicidal or growth-regulating action and then applied jointly.Components in mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, aryloxy/hetaryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-(hetaroyl)/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

Moreover, it may also be advantageous to apply the compounds I, alone orin combination with other herbicides, as a mixture with a further numberof crop protection agents, for example with pesticides or agents forcontrolling phytopathogenic fungi or bacteria. Of further interest isthe miscibility with mineral salt solutions which are employed fortreating nutritional and trace element deficiencies. Non-phytotoxic oilsand oil concentrates may also be added.

PREPARATION EXAMPLES Example 1 (Compound Ia.384 in Table 1)

12.1 g of (2,3-dichloro-5-methylsulfonylpyridine, 11.05 g of4-chloro-2-fluoro-5-methoxybenzeneboronic acid, 13.6 g of sodiumhydrogen carbonate and 2.0 g of tetrakis(triphenylphosphine)palladium(0)were refluxed for 120 hours in 360 ml of a tetrahydrofuran/water mixture(1:1). After the mixture had cooled to room temperature, it wasextracted three times using in each case 100 ml of methyl tert-butylether (MTB). The combined organic phases were washed with 100 ml ofwater, then dried over sodium sulfate and finally concentrated. Thecrude product was purified by means of column chromatography on silicagel (eluent: cyclohexane/MTB=10:1→7:3→1:1). The resulting white crystals(5.8 g) were further purified by stirring with MTB/petroleum ether(1:1). Yield: 5.2 g (27%); m.p.: 184-185° C.

Precursor α: 2,3-Dichloro-5-methylthiopyridine

A solution of 50.6 g (0.3 mol) of 3-amino-5,6-dichloropyridine in 700 mlof methylene chloride was slowly added dropwise at 40° C. to a solutionof 56.6 g (0.6 mol) of dimethyl disulfide and 46.7 g (0.45 mol) oftert-butyl nitrite in 320 ml of dry methylene chloride. The mixture wasthen stirred for 1 hour at 40° C. and subsequently for anotherapproximately 15 hours at approximately 20° C., whereupon 500 ml ofice-water were added to the reaction mixture. The organic phase whichwas separated off was washed once with 1 N hydrochloric acid and oncewith water, dried over sodium sulfate and finally concentrated. Afterthe crude product had been stirred with n-hexane, 21 g of a dark solidwere obtained (purity 94% according to GC). After the hexane solutionwas concentrated, a further 21.3 g of product of value remained whichhad a purity of 77% (according to GC). Total yield: 62%; m.p.: 66-67°C.; ¹H-NMR (in d⁶ dimethyl sulfoxide): δ [ppm]=2.6 (s, CH₃); 8.1 and 8.3(2×d, pyr H).

Precursor β: 2,3-Dichloro-5-methylsulfinylpyridine

8.9 g (0.052 mol) of m-chloroperbenzoic acid were added, a little at atime, to a suspension of 10 g (0.052 mol) of2,3-dichloro-5-methylthiopyridine in 60 ml of methylene chloride. Afterthe mixture had been stirred for 2 hours at approximately 20° C., afurther 0.9 g (5 mmol) of m-chloroperbenzoic acid was added. The mixturewas subsequently refluxed for a further 2 hours. After cooling, thesolids were separated off, whereupon the organic phase was washed oncewith sodium hydrogen sulfite, once with sodium hydrogen carbonate andonce with water. After the mixture had been dried over sodium sulfate,it was concentrated. The crude product which was obtained as a red oilwas purified by means of flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate=1:1). Yield: 6.3 g (58%) as a brown oil;¹H-NMR (in d⁶ dimethyl sulfoxide): δ [ppm]=2.9 (s, CH₃); 8.4 and 8.7(2×d, pyr H).

Precursor γ: 2,3-Dichloro-5-methylsulfonylpyridine

6.2 g (0.02 mol) of Na₂WO₄.2H₂O were added to a solution of 73.7 g (0.38mol) of 2,3-dichloro-5-methylthiopyridine in 380 ml of glacial aceticacid. After the mixture had been heated to 40-50° C., 95 g of hydrogenperoxide (30% strength) were added carefully. Stirring was subsequentlycontinued for a further hour at approximately 20° C. The mixture wasthen poured into 300 ml of water. The product was separated off from theresulting suspension, washed with water and n-pentane and dried underreduced pressure. Yield: 60 g (70%) as a brown powder; m.p.: 129-130°C.; ¹H-NMR (in d⁶ dimethyl sulfoxide): δ [ppm]=3.4 (s, CH₃); 8.7 and 8.9(2×d, pyr H).

Example 2 (Compound Ia.383 in Table 1)

4.15 g of compound Ia.384 which had been obtained as described inExample 1 and 10.2 g of pyridine hydrochloride were heated for fourhours at 200° C. under a nitrogen atmosphere. After cooling, thereaction mixture was taken up in 100 ml of 10% strength hydrochloricacid. The product was then extracted five times using in each case 90 mlof dichloromethane. The combined organic phases were washed with 100 mlof water, dried over sodium sulfate and finally concentrated. Theresulting crystals were purified by stirring with MTB/petroleum ether(1:1). After separation and drying, 3.6 g (90%) of white crystals wereobtained; m.p.: 176-178° C.

Example 3 (Compound Ia.402 in Table 1)

0.52 g of propargyl bromide was added dropwise to 1.2 g of the compoundIa.383 which had been prepared as described in Example 2 and 0.99 g ofpotassium carbonate in 80 ml of anhydrous dimethylformamide. After themixture had been stirred for twelve hours at 23° C., it was diluted with200 ml of water. The product was then extracted four times using in eachcase 100 ml of MTB. The combined organic phases were washed with 100 mlof water, dried over sodium sulfate and finally concentrated. The crudeproduct was purified by stirring with n-hexane/diethyl ether (10:1).After separation and drying, 0.9 g (67%) of white crystals was obtained;m.p.: 182-183° C.

Example 4 (Compound Ia.182 in Table 1; (R) enantiomer)

1.05 g of methyl (S)-2-chloropropionate were added dropwise to 2.4 g ofthe compound Ia.383 which had been prepared as described in Example 2and 1.97 g of potassium carbonate in 100 ml of anhydrousdimethylformamide. After the mixture had been stirred for sixty hours at23° C., it was diluted with 300 ml of water. The product was thenextracted four times using in each case 80 ml of MTB. The combinedorganic phases were washed with 100 ml of water, dried over sodiumsulfate and finally concentrated. The crude product was purified bymeans of chromatography on silica gel (eluent: cyclohexane/MTB=5:1→7:1).Yield: 2.6 g (86%) of a colorless oil.

¹H-NMR (200 MHz; in CDCl₃): δ [ppm]=1.70 (d, 3H), 3.20 (s, 3H), 3.77 (s,3H), 4.78 (q, 1H), 7.00 (d, 1H), 7.28 (d, 1H), 8.33 (s, 1H), 9.07 (s,1H).

Example 5 (Compound Ia.181 in Table 1; (R) enantiomer)

1.2 g of the compound Ia.182 which had been prepared as described inExample 4 were stirred for 4 hours at 70 to 80° C. and subsequently for16 hours at 23° C. in a mixture of 25 ml of glacial acetic acid and 10ml of 2 M hydrochloric acid. After the mixture had been diluted with 100ml of water, it was extracted five times with in each case 60 ml of MTB.The combined organic phases were washed twice with in each case 60 ml ofsaturated aqueous sodium chloride solution, then dried over sodiumsulfate and finally concentrated. The crude product was purified bystirring with n-hexane/diethyl ether (2:1). Yield: 0.75 g (65%) of whitecrystals; m.p.: 161-164° C.

Example 63-Chloro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-methylsulfinylpyridine

4.6 g of 2,3-dichloro-5-methylsulfinylpyridine, 4.5 g of4-chloro-2-fluoro-5-methoxybenzeneboronic acid, 5.5 g of sodium hydrogencarbonate and 1.0 g of tetrakis(triphenylphosphine)palladium(0) wererefluxed for 180 hours in a mixture of 100 ml of water and 100 ml oftetrahdyrofuran. After the tetrahydrofuran has been evaporated, theresidue was extracted four times with in each case 70 ml of MTB. Thecombined organic phases were then dried over sodium sulfate and finallyconcentrated. The resulting oil was purified by means of chromatographyon silica gel (eluent: cyclohexane/MTB=7:3→1:1 and cyclohexane/ethylacetate=2:1). Stirring this purified oil with diethyl ether gave 2.2 g(30%) of white crystals.; m.p.: 117-118° C.

Example 7 Preparation of the Precursor2,3-Dichloro-5-ethylsulfonylpyridine

5 g (0.024 mol) of 2,3-dichloro-5-ethylthiopyridine were reacted with0.4 g (1.2 mmol) of Na₂WO₄.2H₂O and 6 g of hydrogen peroxide (30%strength) in 25 ml of glacial acetic acid by a method similar to Example1, Precursor γ. After working up, 5.1 g of product of value wereobtained as a white solid.

Yield: 88.5%; m.p.: 141-142° C.; ¹H-NMR (in d⁶ dimethyl sulfoxide): δ[ppm]=1.2 (t, CH₃); 3.5 (q, CH₂); 8.6 and 8.8 (2×d, pyr H).

Precursor α: 2,3-Dichloro-5-ethylthiopyridine

24.45 g (0.15 mol) of 3-amino-5,6-dichloropyridine in 280 ml ofmethylene chloride were reacted with 36.6 g (0.3 mol) of diethyldisulfide and 23.2 g (0.225 mol) of tert-butyl nitrite in 130 ml ofmethylene chloride by a method similar to Example 1, Precursor α. Afterworking up and subsequently washing the crude product with ethanol, 13.3g of product of value were obtained.

Yield: 42%; ¹H-NMR (in d⁶ dimethyl sulfoxide): δ [ppm]=1.25 (t, CH₃);3.10 (d, CH₂); 8.15 and 8.3 (2×d, pyr H).

Precursor β: 2,3-Dichloro-5-ethylsulfinylpyridine

4 g (0.02 mol) of 2,3-dichloro-5-ethylthiopyridine were reacted with3.47 g (0.02 mol) of m-chloroperbenzoic acid in 30 ml of methylenechloride by a method similar to Example 1, Precursor β. After the crudeproduct had been purified by means of flash chromatography on silica gel(eluent: cyclohexane/ethyl acetate=2:1), 1.9 g of product of value wereobtained in the form of white crystals. Yield: 42%. m.p.: 78-79° C.;¹H-NMR (d⁶ dimethyl sulfoxide): δ [ppm]=1.1 (t; CH₃); 3.0 and 3.2 (2×m,CH₂); 8.35 and 8.6 (2×s, pyr H).

Example 8 Preparation of the Precursor2,3-Dichloro-5-isopropylsulfonylpyridine

15 g (0.068 mol) of 2,3-dichloro-5-isopropylthiopyridine (crude product)were reacted with 1.11 g (3.6 mmol) of Na₂WO₄.2H₂O and 17 g of hydrogenperoxide (30% strength) in 80 ml of acetic acid by a method similar toExample 1, Precursor γ. After working up and additional stirring thecrude product with ethanol, 3.5 g of product of value were obtained as apale powder. Yield: 20%; m.p.: 146° C.; ¹H-NMR (in d⁶ dimethylsulfoxide): δ [ppm]=1.2 (d, 2×CH₃); 3.65 (m, CH); 8.6 and 8.8 (2×d, pyrH).

Precursor α: 2,3-Dichloro-5-isopropylthiopyridine

13.1 g (0.08 mol) of 3-amino-5,6-dichloropyridine in 120 ml of methylenechloride were reacted with 25 g (0.16 mol) of diisopropyl disulfide and12.4 g (0.12 mol) of tert-butyl nitrite in 70 ml of methylene chlorideby a method similar to Example 1, Precursor α. This gave 30 g of thedark oil (approximately 40% of product of value) which was furtherreacted without further purification. ¹H-NMR (in d⁶ dimethyl sulfoxide):δ [ppm]=1.25 (d, 2×CH₃); 3.7 (m, CH); 8.2 and 8.3 (2×d, pyr H).

Precursor β: 2,3-Dichloro-5-isopropylsulfinylpyridine

10 g (0.045 mol) of 2,3-dichloro-5-isopropylthiopyridine (as crudeproduct) were reacted with 7.8 g (0.045 mol) of m-chloroperbenzoic acidin 60 ml of methylene chloride by a method similar to Example 1,Precursor β. After the crude product had been purified by means of flashchromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1),1.7 g of product of value were obtained. Yield: 16%; m.p.: 62-64° C.;¹H-NMR (in d⁶ dimethyl sulfoxide): δ [ppm]=1.0 and 1.25 (2×d, 2×CH₃);3.2 (m, CH); 8.3 and 8.5 (2×d, pyr H).

Other substituted 2-phenylpyridines I are listed in Table 2 below:

TABLE 2 I

Physical data No. R¹ R² R³ R⁴ R⁵ (m.p.)  1 SCH₃ Cl F Cl OH 164° C.  2SCH₃ Cl F Cl OCH₃ 102° C.  3 SC₂H₅ Cl F Cl OCH₃  94° C.  4 SCH(CH₃)₂ ClF Cl OCH₃ oil  5 SO—CH₃ Cl F Cl OH 163° C.  6 SO—CH₃ Cl F Cl OCH₃ 118°C.  7 SO—CH₃ Cl F Cl OCH₂—C≡CH 145° C.  8 SO—C₂H₅ Cl F Cl OCH₃ oil  9SO—CH(CH₃)₂ Cl F Cl OCH₃ 138° C. 10 SO₂—C₂H₅ Cl F Cl OCH₃ 147° C. 11SO₂—CH(CH₃)₂ Cl F Cl OCH₃ 120° C. 12 SCH₃ Cl H Cl OH 101° C. 13 SCH₃ ClCl Cl OCH₃ 115° C. 14 SCH₃ Cl H OCH₃ H  90° C. 15 SO—CH₃ H F Cl OCH₃137° C. 16 SO₂—CH₃ H F Cl OCH₃ 151° C. 17 SO₂—CH₃ Cl H OH H 226° C. 18SO₂—CH₃ Cl H OH NO₂ 182° C.

USE EXAMPLES Herbicidal Activity

The herbicidal activity of the substituted 2-phenylpyridines I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended oremulsified in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with translucentplastic hoods until the plants had rooted. This cover caused uniformgermination of the test plants unless this was adversely affected by theactive ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of from 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. To this end, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rate of application for the post-emergencetreatment was 0.0313 or 0.0156 kg/ha a.s. (active substance).

Depending on the species, the plants were kept at from 10 to 25° C. and20 to 35° C., respectively. The test period extended over 2 to 4 weeks.During this time, the plants were tended, and their response toindividual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Scientific name Common name Abutilon theophrasti velvet leaf Chenopodiumalbum lambsquarters (goosefoot) Solanum nigrum black nightshade Veronicaspecies speedwell

At rate of applications of 0.0313 and 0.0156 kg/ha a.s., the compoundNo. Ia.384 showed a very good herbicidal activity against theabovementioned broad-leaved plants when applied post-emergence.

USE EXAMPLES Desiccant/Defoliant Action

The test plants used were young cotton plants with 4 leaves (withoutcotyledons) which had been grown under greenhouse conditions (relativeatmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The young cotton plants were given a foliar treatment to run-off pointwith aqueous preparations of the active ingredients (with addition of0.15% by weight of the fatty alcohol alkoxide Plurafac® LF 700 ²⁾, basedon the spray mixture). The amount of water applied was 1000 l/ha(converted). After 13 days, the number of shed leaves and the degree ofdefoliation in % were determined.

²⁾ A low-foam, nonionic surfactant by BASF AG

No leaves were shed in the untreated control plants.

We claim:
 1. A substituted 2-phenylpyridine of the formula I

in which the variables have the following meanings: n is zero; R¹ isC₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; R² is halogen; R³ ishydrogen or halogen; R⁴ is cyano or halogen; R⁵ is hydrogen, nitro,cyano, hydroxylamino, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —COCl, —CO—OR⁶,—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —O—(C₁-C₄-alkylene)—CO—OR⁶,—O—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —OR⁹, formyl,—CH═N—OR¹⁵, —N(R¹⁶)R¹⁷, —N(R¹⁶)—SO₂—(C₁-C₆-alkyl) or—N(R¹⁶)—CO—(C₁-C₆-alkyl); R⁶ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl or C₁-C₆-alkoxy-C₁-C₆-alkyl; R⁹ is hydrogen, C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-alkynyl; R¹⁵ is C₁-C₆-alkyl; R¹⁶ is hydrogen orC₁-C₆-alkyl; R¹⁷ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy; or an agriculturallyuseful salt of a compound I where R⁶=hydrogen.
 2. A herbicidalcomposition which comprises a herbicidally active amount of at least onesubstituted 2-phenylpyridine of the formula I or of an agriculturallyuseful salt of I, as claimed in claim 1, and at least one inert liquidand/or solid carrier and, optionally, at least one surfactant.
 3. Acomposition for the desiccation and/or defoliation of plants comprisingsuch an amount of at least one substituted 2-phenylpyridine of theformula I or of an agriculturally useful salt of I, as claimed in claim1, that it acts as a desiccant and/or defoliant, and at least one inertliquid and/or solid carrier and, optionally, at least one surfactant. 4.A method of controlling undesirable vegetation, which comprises allowinga herbicidally active amount of at least one substituted2-phenylpyridine of the formula I or of an agriculturally useful salt ofI, as claimed in claim 1, to act on plants, their environment or onseed.
 5. A method for the desiccation and/or defoliation of plants,which comprises allowing such an amount of at least one substituted2-phenylpyridine of the formula I or of an agriculturally useful salt ofI, as claimed in claim 1, to plants, that it acts as a desiccant and/ordefoliant.
 6. A method as claimed in claim 5, wherein cotton is treated.7. The substituted 2-phenylpyridine of claim 1, where n=0,R¹=methylsulfonyl, R² and R⁴=chlorine, R³=fluorine and R⁵=—OCH₃.
 8. Aprocess for the preparation of substituted 2-phenylpyridines of theformula I as claimed in claim 1 where R¹ is C₁-C₆-alkylthio, whichcomprises reducing 5-nitro-2-phenylpyridines of the formula V

where n and R² to R⁵ have the meanings given in claim 1, diazotizing theresulting 5-amino-2-phenylpyridines of the formula VI

and finally reacting the diazonium salts with symmetrical aliphaticdisulfides of the formula VII (C₁-C₆-alkyl)—S—S—(C₁-C₆-alkyl)  VII. 9.The substituted 2-phenylpyridine of claim 1, where R¹ isC₁-C₆-alkylsulfonyl.
 10. The substituted 2-phenylpyridine of claim 1,where R⁵ is hydrogen, nitro, cyano, hydroxylamino, C₁-C₆-alkyl,C₁-C₆-haloalkyl, —COCl, —CO—OR₆, —CO—O—(C₁-C₄-alkylene)—CO—OR⁶,—O—(C₁-C₄-alkylene)—CO—OR⁶,—O—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —OR⁹, formyl,—CH═N—OR¹⁵ or —NH₂.